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Cheap Flights from O'Hare Intl to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$361
Santo Domingo
Santo Domingo1 stop$396
Montego Bay
Montego Bay1 stop$448
Oranjestad
Oranjestad1 stop$563
Nassau
Nassau1 stop$397
Kingston
Kingston1 stop$536
Simpson Bay
Simpson Bay2 stops$429
Providenciales
Providenciales1 stop$410
Port of Spain
Port of Spain1 stop$638
Bridgetown
Bridgetown1 stop$578
George Town
George Town1 stop$435
Willemstad
Willemstad2 stops$439
Castries
Castries2 stops$966
Aguadilla
Aguadilla1 stop$210
Puerto Plata
Puerto Plata1 stop$593
St. John's
St. John's1 stop$519
Punta Cana
Punta Cana1 stop$361
Santo Domingo
Santo Domingo1 stop$396
Montego Bay
Montego Bay1 stop$448
Oranjestad
Oranjestad1 stop$563
Nassau
Nassau1 stop$397
Kingston
Kingston1 stop$536
Simpson Bay
Simpson Bay2 stops$429
Providenciales
Providenciales1 stop$410
Port of Spain
Port of Spain1 stop$638
Bridgetown
Bridgetown1 stop$578
George Town
George Town1 stop$435
Willemstad
Willemstad2 stops$439
Castries
Castries2 stops$966
Aguadilla
Aguadilla1 stop$210
Puerto Plata
Puerto Plata1 stop$593
St. John's
St. John's1 stop$519
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Caribbean Islands flights

Get data-powered insights and trends into flights from O'Hare Intl to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Chicago O'Hare Intl Airport found in the last 5 days was to San Juan, at $226 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $226.

What is the cheapest time of day to fly to Caribbean Islands?

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $363 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $524.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Caribbean Islands?

No, with an average price for the route of $532, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Caribbean Islands?

The cheapest month for flights from Chicago O'Hare Intl Airport to Caribbean Islands is January, when tickets cost $554 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $719 and $705 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Caribbean Islands?

If you are looking for a flight deal from Chicago O'Hare Airport to Caribbean Islands, look for departures on Tuesdays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Caribbean Islands, Thursday is the cheapest day to fly and Sunday is the most expensive.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?

To get a below average price on the flight from Chicago O'Hare Intl Airport to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low season

September
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 3% increase in price.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago O'Hare Airport to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago O'Hare Airport to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Chicago O'Hare Airport to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago O'Hare Airport to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from O'Hare Intl to Caribbean Islands

 
Need help choosing which airline to fly with from O'Hare Intl to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10359 reviews
7.1Entertainment
7.7Boarding
8.1Crew
6.7Food
7.3Comfort
Airline reviews

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

10.0 ExcellentAJ, Oct 2026
Read more United Airlines reviews

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Perfect. On time and the weather was perfect so we came in a few minutes early.

On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Our seats were moved for no reason. The plane was old and wifi and tv were slow. The flight was delayed over an hour for a paperwork issue. Only bright spot was the flight attendants good service.

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

The crew did not ensure the Evermore seats had their carry on space available. When my family and I boarded, we saw people putting their carry on suitcases in the overhead spaces above our seats and then proceed to the rear part of the plane. This resulted in us having to check our bags and being late to our meetings/events.

Crew was friendly. Free headphones would be nice. Free new movies would be better.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

The crew was friendly and helpful. The entertainment system in my row did not work for movies and TV shows and the Direct TV cut off in parts and stopped showing the baseball playoff game.

Non-stop commercials were frustrating when trying to view direct TV

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

Great. I was in mint class. Security was spectacular. A lot of room on the flight! And the WiFi worked this time- it didn’t work the last time and I am on a business trip so that was a problem.

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

Better than expected. Staff were friendly and nice on both flights.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Our flight was canceled for no known reason. We weren’t told until we were checking in at 5:00 am. This was after our last flight with Frontier where we sat on the plane for three hours (not an exaggeration) before we took off because of a mechanical issue. We won’t be flying Frontier again.

I didn’t have enough time to catch my connecting flight and had to use a different Airline. I will be requesting a refund.

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental